Leadership + People: Episode 13 - Jane Ann Craig - Part 1 of 2

In this episode Jane Ann Craig talks about her beginning and how as a single mother there was no room for pride. She address the importance of relying on your team and providing them with a clear vision and processes for your business that will protect them and the customer.  

Show Notes

  • How Jane Ann went from receptionist to starting her own company as a single mom [00:46]
  • Expect your plan to take 3x as long, be 3x as hard and take 3x as much [03:26]
  • You don’t need all the answers. Just surround yourself with those who do. [05:51]
  • Have a clear vision that your team understands and can invest in. [10:07]
  • The struggle of being the one everyone relies on. [11:31]
  • Understand where you want to end up and what vehicle you need to get there. [16:53]
  • Create consistent systems that protect employees and clients a like. [20:32]
  • Don’t be one of the 95% of business that fail because they didn’t write their business plan. [23:13]

Show Audio

Show References


This episode of Leadership and People was originally released on: November 22, 2017

Show Transcript

[BEGINS] 00:00

Welcome to Leadership and People. This is a series that pulls back the curtain on leadership by interviewing CEOs, Senior Executives and Entrepreneurs who had large exits. We ask these experts about how they built trusted networks to rapidly grow their companies.  And what advice they wish they knew if they could do it all again.

HOST – JESS LARSEN: Today on the show we’ve got Jane Ann Craig.

GUEST – JANE ANN CRAIG: “Too many people have lost themselves in their jobs. They forget why they work. They forget why they started their companies. They started it to have a certain lifestyle and then they end up divorced. They end up not being there with their children. And so I always looked at my company as a vehicle to support our goals our dreams and our visions.”

00:17 JL: Jane Ann thanks for making time.

JANE ANN CRAIG: Thank you Jess.

00:46 JL: So, I think you’ve got a fun story. Kind of the unlikely entrepreneur story. Can we talk a little bit about where you started before you ended up you know growing these big business you sold to national insurance Blue Cross Blue Shield.

JANE ANN CRAIG: Sure sure. Just want me to go back to…? Ok. So I… I started working- we’re talking my career right now right? Okay. I started working for a dental insurance company when I was going to college. It was simply a job that was close to my college. That allowed me to work and go to school at the same time. So I would go to work, race to class, race back to work. So it was very very flexible. And I worked for that company until I graduated. And when I graduated my boss said what would I like for my graduation present. And I said I would like to start my own company. And so he was just opening up operations in Bismarck North Dakota. We were in Southern California. Nobody else volunteered to go. So that was my big break. So I went to North Dakota.

01:47 JL: Can you talk about why you needed to start a business and the whole genesis of being widowed and..


01:58 JL: …and providing for a 2 year old.

JANE ANN CRAIG: ok so. That’s where I got my skill. Is I started working for a company while I was going to college. Started as a receptionist and then moved around with them a little bit and they moved me to Utah ultimately. Met my husband my first day in town. Continued to work for this company. And then very unexpectedly my husband was diagnosed with advanced stage bone and lung cancer. And 8 months later he passed away. So now I find myself a single mom. I am the sole provider of a 2 year old son. And I stayed with the company for another 3 years until I realized that the company no longer supported our goals our dreams and our visions. And it was a great company. It was promoting me. They were expanding my territory. But it no longer supported me being a present, engaged mom. It no longer supported the dreams we that shared as a family. And so It meant time to make a decision. It was kind of the only thing I thought I knew to do. So I decided to quit and start my own company. And dental insurance was it.

03:11 JL: And how many companies did you end up with all together?

JANE ANN CRAIG: Ended up building 4 before it was all said and done. So we had two dental insurance companies. One in Utah. One in Arizona. And then two service companies.

03:26 JL:  That’s great. So how many years from starting those businesses before you built your multibillion dollar business that you sold to the multibillion dollar business?

JANE ANN CRAIG: My business plan said it would take 3-5 years. It took 15 years to sell. It took a lot longer. People always say it takes 3x as long, 3x as hard and 3x as much. That was probably accurate for me. But I was learning as I went.

03:54 JL: And then you stayed on once you sold.

JANE ANN CRAIG: I did. So the contract- and this is typical of most big acquisitions, is that we agree to stay on for 2-3 years. I stayed on for 3 years and then I was asked to go ahead and just stay on. Which I did for 2 more years. And I’m glad I did. I can say I’ve been a CEO in a multi billion dollar enterprise. Which is cool. And I learned things which we were striving to achieve. But it was a national company, a federal contractor and it was not the same as being an entrepreneur when you shift from building a company to becoming a very institutionalized institution. We were one of, I think they had over 20,000 employees. So the dynamic changed fairly quickly.

04:43 JL: No kidding. And then tell us about your consulting company now.

JANE ANN CRAIG: So- The fun thing in starting a company is that we make just about, or at least I did, make every mistake you can possibly make. And so what that means for my clients is that I learned from my mistakes and so whether it was regulatory, whether it was shareholder issues, whether it was employee issues. Things that we see because we have done it but other startups, other entrepreneurs, if they have not yet, you know, hit some of those obstacles. They don’t even know there’s a red flag. They don’t even know that they are treading in the danger zone. And so what I get to do is, I get to sit down serve on boards, serve with other CEOs, some startups, some very institutionalized, and help them navigate some of the challenges that they are going to face. And maybe let them learn from my experience.

05:45 JL: And tell us the website.

JANE ANN CRAIG: The website is janeanncraig.com

05:51 JL: So I want to talk about the name of this show is Leadership and People. And definitely talking about you know, Corporate Alliance. We are both obviously apart of the C4 group. When you think about the role of you know doing good work plus knowing the right people to do that good work with. How have you seen networks grow the businesses you grew?


06:16 JL: Or networking or building relationships?

JANE ANN CRAIG: Yea. So I got involved with Corporate Alliance probably about half way into building my company from start to acquisition.  It was a game changer for me. It literally was a game changer for me. In fact I think that I was very purpose driven. And so I would have sold the company and I would have done well. But I learned so much as a result of corporate alliance. And the people that I met. Really for the same reason I’m consulting today, I learned from other peoples relationships. I learned from their mistakes. I learn from their creativity, their innovation. So from almost the beginning of when I joined Corporate Alliance, the vendors all became fellow Corporate Alliance vendors. My coaches, my mentors became Corporate Alliance members. And so even the books that I read were life changers for me. So I did not have the benefit of a business degree. I didn’t have accounting classes and yet I’m CEO’ing a highly regulated financial institution. I was able to surround myself and benefit and be encouraged by other leaders. It has been huge for me.

07:28 JL: Yea. Thinking about growing your own talent, you know leadership and people inside your organizations. I think most of us who have started something or run things, we have all these theories about how it’s going to go and then you start working with real people. [laugh] Right?  And you’re like this is different than when I was the peer. Now as the boss sometimes it’s not exactly as you imagined. What are some of the things that you latched onto that kind of became your way of growing leadership in your people?

JANE ANN CRAIG: One of the things I am probably most proud of in building my company is that-  I started, I didn’t have any money. You know I’m a single mom with a two year old. And so I had to start and I had to start quickly. So I hired my babysitter. I hired my karate teacher. I hired the guy who flipped burgers at McDonalds to build our software. And so we hired really talented young people and then allowed them to grow. And today’s CEO of that family of companies, when he started working for me he was like 19 years old. No college degree and yet today he is the CEO of a multi multi million dollar company. And so I’m super proud of that. So I guess if you are saying what would be one of my…

08:50 JL: Or what are principles that the rest of us can learn from? ….. You know, one thing that I found is: you’ve got to give people enough rope, but not so much that they hang themselves.


09:00 JL: Whatever your version is.

JANE ANN CRAIG: Well I’ve surrounded my entire career, even what I’m doing now, I’ve surrounded myself with young people that are creative. That certainly understand technology better than I do. They have a lot to prove. That like to be taught. That want to be given the opportunities. So I think as you mature you have to have the CPAs. you have to have the lawyers. You have to have those skilled people. But my story is we built a multi million dollar company with a lot of young people. Some who didn’t have high school diplomas. And grew into amazing leaders. And so I think my job was to invest in them and then to lead them. I believe in a servant leadership. I believe in being an example. And sometimes demanding, but teaching throughout the whole process.

10:00 JL: When you think about that balance, sometimes setting the bar you know


10:07 JL: Or letting people know this isn’t getting the job done. But from you know a servant leadership attitude. How do you walk that balance beam there?  How do you balance the “if I don’t say anything I’m letting the company down. If I indulge in feelings of blame I’m probably not being a great leader? How do you walk the line in between?

JANE ANN CRAIG: Well it’s easier when you are not desperate. So in my first many years, if we didn’t make enough money my employees couldn’t get paid and certainly I couldn’t get paid right? And so I was pretty straight forward. I do believe in encouraging and not talking down. I believe that our employees have a lot to offer. I believe as leaders it’s our job to cast the vision, to allow our employees to help execute. And then we tweak it. and we guide it and we correct and we point out why, so that we learn through every experience we take on. I mean there’s no doubt as founder of the company, at the end of the day it fell on me. But I really really relied on my employees. I really relied on them. And I think most of them knew that. If that didn’t they didn’t stay. Does that make sense?

11:26 JL: Sure


11:30 JL: You know I think there are so many opportunities for leaders to sometimes feel special.  Like we’re a big deal because staff know that we pay the paycheck. Or especially if you start getting financial people start to treat us different. So you know like for me when I was a young, when I first became a CEO and you know I’m 28 years old running a private equity fund I kind of wanted- If i’m honest about it now, I kind of wanted to be a big deal. You know I wanted to prove to all those high school jocks that didn’t think I mattered, that I matter. And there’s-  You can get away with a lot of more self focused behaviors when you’re wealthy and in-charge. And fortunately I had some hard lessons to learn about humility, you know. For somebody who wants to humble themselves instead of be humbled by life, any advice on how to take a look in the mirror as a leader?

JANE ANN CRAIG: That’s a tough questions. Most of my career I was struggling to build my organization and to take it to an acquisition. I had employees that were relying on me. I had shareholders that were relying on me. I had regulatory agencies that were requiring of me. And I always relied on my employees. I never had the luxury until I sold my company to let my guard down at all. And so I don’t know if that was an issue for me. But I would say this is that one thing I learned, for example when I raised capital for my company, that the people who put the money up were the people who had been watching me. They were the people that saw the mistakes I made. They saw how I handled the mistakes I made. They saw how I treated people. They saw how I navigated challenges. They saw my tenacity. And so I don’t think we ever take advantage of the people who help us succeed. I just don’t think we ever do. I think that we need to be willing to shift and self correct. And I’m not sure if I’m answering your question. You know my situation was a little different from the standpoint that I was a single mom that had put everything on the line and there just wasn’t a lot of room to fail. And so really relied on my team. I just really relied on my team. And to this day I am very very grateful to them.

14:08 JL: That’s such a great story. I want to talk about this principal tenacity that you brought up.


14:14 JL: You know being an entrepreneur is cool these days.

JANE ANN CRAIG: It is. It is. It’s very hip right now.

14:21 JL: Right? And we certainly… You know there’s an author I really love from Texas named Austin Kleon. And he talks about- there’s a lot of people who want the noun without being the verb. He’s talking about being an author. They want to have a book written. They want to be a published author. They don’t necessarily want to write the book.


14:43 JL: And so there’s a lot of folks who maybe fall into the “wantrapraneur” category, right?


14:51 JL: And then there’s folks who don’t seem any more qualified that do seem to have the tenacity to pay the price to take all the skinned knees it takes to learn the skill set. Right? When you think about, let’s talk about people again here. As you are selecting the kind of people you want on your team, how do you identify somebody who you think is actually going to bring that type of tenacity to the organization versus someone who just interviews well?

JANE ANN CRAIG: In the early years of my company I hired everybody. You know I hired people that I knew, that I knew would be loyal. I think I choose that more than anything. That would represent me well. That were teachable and trainable. As my team grew I realized that I wasn’t necessarily the best interviewer. And so we had a process. I would have typically maybe 5 employees on a hiring team. And they would vet the employees. And they would get it narrowed down and then it would go down to a couple employees. And then I got to make the final decision. And often times I would pick up on concerns that maybe the staff wouldn’t. But there were other times my staff would argue that this person was worth taking a risk. And if they did then I would usually acquiesce because I figured they saw something that I didn’t see.  That system worked really well for us. Now once we sold and became a Blue Cross company. Then again it’s like the federal government. There were assessments and testing and we didn’t have that same kind of control. I think at the end of the day I think it really hurt us. Because what built the company was a sense of investment. A sense of commitment. A sense of ‘there’s no ceiling to this company’. And so again I relied a whole lot on the team.

16:53 JL: That’s great. What’s another leadership principal? What’s something else you think helped you get to where you got to?

JANE ANN CRAIG: So I…. I have a… I mean I have several life philosophies. Probably the life philosophy that I spent a lot of time talking about right now. And we talked about it a little bit before we got on the mic and I’ll just , I’m not going to give the title or anything but I’m writing a book on it right now. But I think one of the keys to success is- its understanding where you are, but it’s understanding where you want to end up. And most people they don’t end up with their goals or their objectives or their dreams because they are non-intentional in going after them. I look at our companies, I look at our jobs, I look at our decisions, like vehicles. And so when I started my company it wasn’t because I dreamed of being an executive. It was that I wanted to be there for my son. I wanted to be generous with my life. I wanted to be a woman of influence that could support causes. And so I took a step back and said “What vehicle is there that will allow me to be have the flexibility and the resources to be there for my son, that will give me a position of influence in the community, that can give me the resources that will allow me to support causes. And what is the vehicle that will get me there and will get me there the quickest. And so I look at our jobs and I see too many people have lost themselves in their jobs. They forget why they work. They forget why started their companies. They started it to have a certain lifestyle and then they end up divorced. They end up not being there with their children. And so I always looked at my company as a vehicle to support our goals our dreams and our visions. So when I talk to business people, you know my first question is “what’s your purpose”. I liken it unto when we take a vacation cuz we get this. When we take a vacation we always start with the end in mind. You know with our destination. And then we take into consideration our purpose. Is it that I want to go to the beach and just chill out and relax? Is it that I want to take my kids to museums? We understand our purpose of the vacation. Then we understand our starting point. And then we take into account our budget, our time line, and what vehicle is that vehicle that makes sense to get there. We know if we are going to Hawaii we need a different set of vehicles than if we are going to Disneyland. We totally get that but we don’t approach life that way. We don’t approach our decisions that way.  And so my advice to business people is whether it’s an individual process or whether is a big goal or big dream; what’s your purpose? What’s your timeline? Now we can talk about what’s the best vehicle to get you there. Then we’re doing what Michael Gerber says. We are working on instead of getting lost working in. So that’s been real helpful to me.

20:13 JL: You know it’s interesting those E-Myth books from Michael Gerber. How…


20:17 JL: Sometimes in big business people dismiss those methodologies “Oh those are for small businesses” But when you go down the list [laughs] many many large businesses still have holes in exactly the same places right?  


20:32 JL: That systematic approach of reliably being able to provide services that exceed expectations just seems like such a recipe for success doesn’t it?

JANE ANN CRAIG: His concept of the french fry. It tastes the same everywhere in the world because McDonald’s provided systems and processes to their employees. I can’t tell you how many CEOs including myself that that was a total Aha! moment. It was like, I think back in the early days of my company, and you were kind of darned if you did and darned if you didn’t. If you were a sales person you’d want the french fry to be crisp and have this much salt. If you were an accounting person you didn’t want it to cook too long. And I felt so sorry for our customer service people cause they never could have the right answers, cause we made so many exceptions. And so it’s a balancing act knowing how, you know how do you be customer service friendly. How do you make every experience tailored and customized and make the customer feel that they are special, while at the same time giving your employees the processes and the systems so the outcomes can be predictable and cost efficient. It’s a big aha moment for most of us.

21:49 JL: Well it’s funny, you know, talking about fast food is almost like a cliche thing to do in the entrepreneurial world. But yet how many of us have not master it, right?


21:59 JL:  Do you know what I mean. Like maybe you are tired of hearing about it but it’s not like you’ve done it [laughs].


22:03 JL: For so many of us right? I like, do you know Guy Kawasaki. Guy used to work for Apple.


22:09 JL: He says people come to him all the time with these business ideas. And he stops them you know when they say they have a better product. He’s like “yea. Listen let’s talk about hamburgers for a minute. Do you think you can cook a better hamburger than McDonalds? If you just started with hamburger, it would be a better hamburger than McDonalds. But do you think you can build a better distribution system than McDonalds. Because that’s what I want to hear about. I don’t want to hear about a better hamburger. I want to hear about you know a better distribution system than them that even teenagers can’t break.


22:36 JL: Right.

JANE ANN CRAIG: Well and … that may not be the cool part that we talk about as entrepreneurs. We like to talk about leadership. We like to talk about employees. We like to talk about culture. But the day that you start thinking about your exit strategy, you start thinking about profitability. You start thinking about profit margins. And by the way, if you’re really going to protect your employees, you’ve got to give boundaries. And you’ve got to give them processes. You’ve got to give them something that makes them safe and able to function. It’s just a part of doing business.

23:13 JL: Yea. I wish I could remember  who I’m plagiarizing here but there’s a quote I heard of clarity equals kindness. You know when staff knows what the front of the puzzle box looks like it’s sure a service we can give to them.

JANE ANN CRAIG: Yea. Absolutely. I think that one of the strongest characteristics we have as a leader is for us to get our vision just as clear as we can. And yes we have to be able to communicate it so that our employees and our vendors and everybody that’s involved, can run with it. We have to do that. But I’ll take it a step further. If you can’t write it down it probably doesn’t exist. And so most CPAs will tell you that 95% of business fail because they didn’t take the time to write down a business plan. But that’s a key to success. It just is. It’s not necessarily, you know, a real fun part of it but it sure keeps you safe and it addresses all of the issues we are going to face.

24:25 JL: Love it. I think this is a great place to stop for part one of the episode. Everybody tune back in. We’re going to ask Jane Ann for some more of her secrets for success.

[END] 24:33